The Challenge: Dragon Sex
by The Love of Our Lust
Summary: The logical steps that lead to mating with a dragon. NO ANTHRO. BE WARNED. ToothlessxHiccup. One-Shot. RATED M FOR MATURE.


**A/N:** Hello, this is Dead Wang Toys from **The Love of our Lust**. This is actually a ficlet I had in mind for months for our very own Pleasnt Prodding Spike. She quite liked. I hope you do too… you pervs. XD

**WARNING:** This is explicit material of DRAGON ON BOY SMUT. Indeed. NO ANTHRO HERE. Total and complete bestiality. Youngsters, please click the back button. Those squeamish or with serious morals, I advise you to not read. ****

**DISCLAIMER: **I hate this part… This writer owns nothing but the clothes on her back… and that's about it. Srsly.

**SUMMARY:** The logical steps that lead to mating with a dragon.**  
><strong>**…**

The Challenge: Dragon Sex

Hiccup thought a lot of things wouldn't happen in his lifetime. One, he thought there was no way he could befriend a dragon. Two, he thought there was no chance Astrid would ever speak to him of her own volition. Three, he thought there would never be a time when he could honestly speak to his father. Mostly he thought he might never fit in with his Viking clan, barring the normative death by fiery mayhem.

Yes, Hiccup could be a tad bit fatalistic.

Well, in the end, he was severely wrong. It just goes to show how very wrong a single view could be.

That being said, while there were many things Hiccup thought would never happen, there were some situations he just didn't give a thought to in the least. One of these was the possibility of a sexual encounter between him and Toothless. Again, Hiccup had a history of being corrected.

It was not like the idea randomly or suddenly popped into his auburn head overnight either. This was a very subtle outcome. Extremely subtle. It happened in stages.

The first stage? Words.

"Toothless sure loves you, Hiccup…" Astrid commented out of the blue.

They were sitting on a grassy knoll that time, she sharpening a battle-axe, and he sketching in his notebook. It was one of the rare warm, lovely days. The sun was shining; the clouds were fluffy and pristine like soft snow in the definition of a sky blue sky. He hadn't quite been paying attention to the buxom blonde, so her fist reached out and tapped his shoulder harshly. There would probably be a bruise later from such a hit.

"Ow! What was that for?" he asked, grimacing as he rubbed his tender shoulder.

"You weren't listening to me!" she loudly declared. Hiccup contained the urge to roll his eyes.

"Yes I was!" he argued, despite the fact his eyes were trained elsewhere. Toothless was bounding amongst the tall green grasses, in the process of catching butterflies.

"Well, what did I say?" Astrid inquired. She was glaring at him, running a cutting stone along the shiny edge of her chipped blade.

"Uh…" he began, the uneasy glances caught between the blade and the frolicking Night Fury.

"Yeah, that's what I thought…" she muttered. There was a high-pitched _zhiiing!_ as she swung her axe off to the side, testing the way it sliced through the air. Hiccup gulped, shrinking back to the scribbles in his notebook.

"Well… sorry," he apologized. Astrid sighed, returning to the gleaming axe she held with bizarre ease. He waited, wind rushing past them, playing across the grass like a rolling emerald wave. Toothless popped up, large paw-like claws coming together to capture an unsuspecting monarch. The redhead felt sorry for the thing until the dragon peeked inside his claws. The yellow-black wings fluttered, and the butterfly was now resting on his crinkled nose.

"Awww, cute!" Astrid cooed. Hiccup turned to her, staring at her incongruity. She found a dragon chasing butterflies adorable, yet was in mid-repair of an axe he was fully aware she had already used to bloody several foes.

"Astrid?" he asked, shaking his head to rid the thoughts that threatened to confuse him.

"Yeah?" she responded coolly.

"Are you going to repeat what you said?" he questioned.

"What did I say?" the blonde asked in return, looking to the cottony clouds, trying to recall her previous statements.

"I dunno, that's why I asked," he said. Toothless sneezed somewhere behind him. There was a sudden thud that momentarily sent the ground quaking under them.

"Oh! Yes, that's right. I remember now," she said smiling. She laughed to herself—which was creepy in and of itself, but it worsened as she swung her axe in a criss-cross pattern before persisting with sharpening it further.

"_Sooo_…?" Hiccup tried.

"So what?" Astrid inquired in such an innocent way; he actually believed she was sincere.

"So, are you going to repeat what you said so I know why you hit me?" he asked, exasperated. Toothless was stomping over to them by now. A bright butterfly wing was conspicuously hanging out of the side of his mouth, and is expression was clearly cheerful. When he reached the two humans, he batted his large, flat head into Hiccup's slim side.

"Nope… Not repeating."

"Seriously?"

Astrid wasn't the only one who noticed. It ranged from the nerdy Fishlegs to the oblivious twins to even his fight-first-ask-questions-after-the-slaughter father.

This happenstance was during dinner. Toothless was eyeing the plates of fish on the table; his tail swishing every time Stoic grabbed another smoked cod. He licked his lizard lips, bending his head down to Hiccup's lap in an impatient manner. The redhead just scratched him under his chin while he calmly chewed his dinner. The tail swishing ceased, and a low rumble came from under the table. Stoic sent him a weird look.

"That black devil trusts you. He really is yours, isn't he?" his father commented more than asked. Hiccup didn't know what to say to that. He just handed Toothless the remains on his overloaded plate. Luckily, his dad just continued to finish off the rest of the meal be himself, changing the topic to something else.

What the two closest people in his life said must have profoundly affected him, subconsciously or otherwise.

This lead to the second step: Pure Curiosity.

"I wonder why you are the only Night Fury around here…" Hiccup questioned one day. He was washing off his leather saddle in the pond located at their secret grotto. As he dipped a brush in a hardening solution to spread it across the saddle to keep it in top condition, he glanced up to Toothless. "Did you migrate here? Are you the last of your kind?" The dark creature looked up from his rock overlooking the crystal clear waters. He sent Hiccup a purr, almost as if he was unconcerned with the idea.

The Viking Prince did not appreciate it. He was unsure how the dragons reproduced. What if they had a mating season? What if they all mated at different times? Different rates? Would it been ritualized, or once in their generation, like the way a salmon spawns? What if Toothless was a truly endangered type of species? Was it not Hiccup's obligation to help repopulate Night Furies? How did they even breed, anyway?

From that moment, Hiccup began to do research. Any and all books that the village had on dragons and their histories and the Viking accounts of dragon nesting—inaccurate as they more than likely were—he took for himself. He scoured every source, but could find nothing.

He spoke to all the elders of the village. They could only tell him so much, and even that was tainted by the old ways of thinking and acting with a prejudice against dragons. Any helpful information he could glean, he kept in a careful and detailed record.

The next step was flying with Toothless as far as he could go in a day without stopping. They flew in every direction, taking maps and watched the scenery, drafting and revising the landscapes in his packed notebook. A cartographer would have been jealous, or would have jumped at the chance to make him an apprentice… Unfortunately, after attempts so numerous he lost count, Hiccup discovered no Night Fury nest, or even another Night Fury like dragon.

Heavy hearted, but knowing he was defeated, he abandoned this quest. He was as clueless as the day he started. Plus, Toothless wasn't lonely. Not at all. He seemed truly content. Down right excited most days.

"What a silly adventure that was, huh, Toothless?" Hiccup rhetorically said, relaxing on a cliff. The ocean was butting against the rocky face of the summit, the waters leaping forth, salting the air. "You aren't unhappy at all…" With a playful growl, Toothless pushed his smooth and scaly forehead into Hiccup's too hot palm.

The next step was a series of natural occurrences.

Hiccup was still a growing boy. Certain hours of the night, he would awaken, feeling a stirring in his nether regions. In the dark he would vaguely be aware of the bulge highlighted underneath bundles of sheets. He was aware it was natural—his father and Gobber took time to explain the birds and the bees. Not that he understood what bees and birds had to do with copulating. Still, he knew the longer he ignored the light throbbing in his loins, the more likely someone like his father might walk in, simply because he had awful luck like that. What he was going through was awkward enough.

Slightly tired and sore, his knees rose up. He parted them, the coarse blankets stretching across the peaks, hiding his future movements. From there, his hands trailed over his fluttering stomach, then beneath his trousers.

It always startled him when the light pads of his fingers found the flesh of his penis. It was sturdy and ready. The air around him would become balmy, and Hiccup found himself breathing it in as deeply and even as he could. He fondled himself in a drawn out rhythm, enjoying it privately. His eyes closed, being as secretive as possible. It would completely mortify him if his dad knew he did this on a semi-regular basis.

As the sensations swelled, the tempo quickened. Hiccup felt the end drawing near. A tiny sound escaped his plump lips. He had to shift in his bed, hips swaying, wiggling. It was drawing closer. His fingers twitched and he gripped just the slightest bit harder. The friction aided in tipping him over the edge.

"A-_Ahhh…_!"

He came in spurts, wetting his hand, and dampening his nighttime clothes. The redhead slackened, falling back into his mattress. His legs flattened and he lifted his hand up, licking experimentally at the white substance coating his fingers. It was salty, and strange on his tongue. Not unwelcome, but nothing superior to the taste of anything else.

After he wiped his appendages clean on his dirtied pants, he scanned the room somewhat sleepily. Finally settling in bed, he yawned. He blinked several times, eyes traveling to the ceiling. A reflective green gaze was aimed down at him inquisitively. Normally, the redhead found the intelligent stare of Toothless rather intriguing, but tonight it distressed him when he realized his midnight activities must have woken the dragon. Just then, Hiccup found himself paralyzed. He didn't know if he should go to sleep, or explain what he had done…

In retrospect, those thoughts were silly. Yes, Toothless was a smart creature, but he was not human. He did not have the same mental capabilities… right? Hiccup was unsure sometimes. That night was one of those brilliant instances in his mind.

As Hiccup lay there, blushing red as a tomato, Toothless did nothing. He blinked a few times, each time his pupils dilating and contracting faster than the previous time. It was as if Toothless was trying to seek an answer, observing his master until he understood what he witnessed. After a span that seemed to encompass hours, the dragon closed his eyes and turned away, ending the heart pounding uncertainty of what to do _now_. Hiccup only relaxed when he fainted from holding his breath for so long.

In the following morning, Toothless acted no different than before. From time to time, though, he would watch Hiccup when he was lazing about, almost as if the poor thing was still puzzled. No other person—dragon or Viking—took note of this.

Though, Hiccup was alert for subsequent performances, he was still worried about waking Toothless. When the need to touch himself and relieve the tension in his lower body came back at night, he disregarded it. The solution he came up with was squeezing his legs together, and squashing himself to the mattress instead. It took several weeks of these occurrences before he couldn't take it anymore.

Biting his lip, he swept his eyes around the room furtively. Toothless was lying beside his bed this time. Particular nights, he was close by Hiccup. It was like he sensed a buried need for comfort or company within his master. It was something the Viking Prince was grateful for… well, on any other night he was grateful. Stealing another look, he saw the ink colored midsection was rising and falling, unstressed and consistent.

Throwing caution to the wind, Hiccup leaned back in his bed, lifting his knees enough so that they opened a space for his hand to dive into his trousers and grasp his aching manhood. He was too preoccupied to leisurely work the needy organ in his usual methodically developed routine.

The redhead promptly stroked the silky shaft, gasping at the intense wave of pleasure that hit him. He had to bite back a scream as he continued the ruthless attack on his own hapless cock. It had been a while, and he had never dared to do this so recklessly. That had to be the reason he could feel a white hot fire churning his insides, liquefying his brain.

It was going to happen, soon. He was going to complete this fantastic, dirty thing he was doing. He was so close to the boiling point, he wasn't paying attention to what he was doing—thrashing, making inaudible noises. It should have only been a tiny sound. No one could hear it, and if they did, they might assume they imagined it, or it was a mouse.

Alas, the terrible luck that is Hiccup's dictated that it would be heard. That tiny noise of his turned into a full squeak of minor terror when his bed was suddenly nudged. Instantly, he halted his actions. The already racing heart nearly exploded. Something had bumped his bed into the wall. With surprised eyes, Hiccup looked over to the source of the disturbance.

A dark reptilian head was resting atop the mattress.

"T-Toothless?" Hiccup hissed, his hand leaving his pants guiltily. With determined eyes the dragon crawled up into the bed. Upset, he heard the sounds and thought the poor boy was in pain. The bed was sunk almost to the floor, and Hiccup scooted so he wouldn't be crushed by the insistent Night Fury.

No matter the reassurances Hiccup gave him, the scratches or orders to hop down, Toothless refused to dislodge from his spot beside his master. That night was internally hectic for the poor redhead. He didn't finish, and really couldn't, having to wait out the soreness. The furnace of the large body next to him did nothing to ease the swelling of the southern half of his body. It was a sleepless and troubling night for both parties. Any chance of having a single bed had been dashed that very same night.

This led to the final step. It was an accident that escalated to the impossible.

He's not quite sure what happened, but Hiccup was flying with Toothless; just suppose to be a regular flight. Dad wanted him to patrol the area. He was worried about neighboring villages, because the temperature dropped drastically overnight, and when that happens Vikings pillage for what the can't find in their homes. As the next chief of the clan, he had to be ready for things like this. It was the perfect opportunity for him to be on the look out and tough. Bold. Brave.

That stuff that might be great for legends and ballads, but that day, the wind was bad and icy. The sky and sea were gray as ash, blending and tricking his eyes. He knew that up could be down and down could be up. So, shivering and clutching to Toothless, he let the dragon utilize his instincts. They were drifting with the wind for a while… they must have been high up, because Hiccup was lightheaded and had to suck in a bit of air at a time, releasing it slowly. It was hard to think, much less keep his eyes open.

"T-This is too dangerous, Toothless," Hiccup chattered, speaking over the blistering wind. "We have to head home!"

Toothless nodded, his intelligence as astounding as his agility. One wing tilted, and Hiccup worked with the pedal to guide the back fin into the correct position. It was executed perfectly in tandem. They were the ideal team. One with out the other was impossible…

But the weather was angry, or perhaps Odin was testing them, because within mere minutes, the air currents went wild. Hail was bombarding the pair, and the sky was awash in noise and electric blue light. Somehow, they backtracked into a storm. It must have been right behind them since they left Berk.

Spiraling out of control, Hiccup and Toothless were plummeting. The dragon was squirming, trying to right himself. Hiccup's tether broke, and he couldn't reach his companion alone. He called out, flailing, feeling a sense of dread and helplessness overwhelm him. Green eyes zeroed in on the scene—a scene he hoped to never relive.

Hiccup fell too fast to stay conscious, only barely recognizing a volcano-hot body closing around him.

By the time he regained his senses, he could smell saltwater and fresh winter rain. There was coldness around him, but it could not reach him. No, he was caged in a black-scaled sanctuary. Leathery wings were folded over him, and when he shuddered, it was at how the dragon was cradling him. The strong, formidable legs were intertwined with his, and the front claws were scraping the top of his damp scalp. Toothless kept breathing his dragon-fire breath over him in huge, hyperventilating puffs. Hiccup's fingers twitched, pressed against the leveled scales of a dark lower belly. It was the oddest feeling, but the redhead would rather not move. He wanted to stay like this until Ragnarok…

But Toothless whined, pushing his nose across Hiccup's neck, and even though it tickled, when the dry heat of his breath grazed Hiccup's ear he moaned. Such a reaction was more than embarrassing, but the dragon didn't understand it. Toothless nuzzled into the human, his impossible embrace tightening.

"I-It's okay…" Hiccup soothed, his eyes peeking open. All he saw was seamless black. Slowly, he could pick out individual scales; they were glossy—wet from the ocean waters. He was not sure how Toothless could survive in such extremely cold conditions, being cold-blooded and all, but the heat generated from deep inside the creature seemed to keep them both sustained until help could reach them.

Toothless blasted off his lightening like fire, beaconing their village, hoping their rescue eventually comes. The dragon never released his master from the shield his body created. Astrid was the one who found them first. She swaddled Hiccup in the heaviest blanket to be woven yet, and made him ride in front of her on her dragon. Poor Snout was the one who had to get Toothless home. His Monstrous Nightmare was flaming, sustaining the agitated Night Fury in it's talons.

They arrived home, and Gobber replaced the broken back fin, saddle, and pedals—much to Toothless' distaste since Hiccup was quarantined to bed rest. The dragon was restless and snappy, and when Hiccup heard about it from his friends he worried. It took a few days after that to placate the village that his delicate sensibilities were quite well repaired. Toothless was very pleased.

They went to the grotto as a reprieve. There, sitting along the sandy soil, Toothless came right behind Hiccup, and expelled a distinct sigh. Smiling softly, the redhead turned slightly to him. "Worried, boy?" he asked. Toothless leaned down lightly, and his flat tongue came out and licked the side of Hiccup's face. The Viking laughed lightly, rubbing his cheek. Toothless licked him again. Shaking his head, Hiccup just patted the dragon's forehead. "I know. I'm fine…" he murmured.

Toothless snorted. His knowing stare was trained on the naïve human. The third time his tongue licked Hiccup, it went from the jaw to the corner of a parted mouth. "Hey, stop it, T—" wide-eyed, the redhead was cut off when the dragon pounced, front claws digging into his shoulders as he pinned the meager human into the malleable earth. It was reminiscent of their first meeting. "_Ahhh_!"

The Night Fury was tracing the femme curve of Hiccup's pale neck. The rubbing along the path, the sizzling puffs of breath were ruffling auburn strands temptingly. The claws were retracting and then releasing into the fur vest, kneading like a feline. Hiccup found himself becoming slowly aroused. Fidgeting, he tried to somehow liberate himself from his companion. There was a growl as Hiccup moved, shimmying his shoulders in an effort to flee.

He yelped when a nip to his collarbone was the response. It didn't hurt. The sharp teeth of the reptile barely poked through the several layers of clothes. Toothless was only warning him. Nonetheless, there was a thrill that came with the option of danger, of pain. It made his nerves flame to life. Hiccup stilled, closing his eyes sympathetically, allowing their contact to continue.

"Alright, Toothless… You have me right where you want me…" he admitted. He gave in. The thoughts he did not realize he could have flooded his mind. Toothless continued licking, nestling, and biting where he deemed needed his attention, shredding the fabric hiding Hiccup from his wondering eyes in the course of the exploits.

The redhead was covered in blossoms of purple and blue blemishes that yellowed around the edges. Hiccup was alarmed that he enjoyed the treatment, little whimpers bubbling out of him. Every time, Toothless would pull back, tilting his head at his master. Hiccup would nod, flushing lightly. Toothless would continue.

Hiccup had glanced down, feeling a new heat exposing itself to the world. Emerging from an indiscernible slit of the dark armor covering the lower part of the dragon was the tip of his penis. It was the palest pink, like a seashell, and looked softer than it should have been. It slid out dauntingly, thick and shiny. The human did not know what came over him, but he knew he went to touch it, a terrible desire to simply _know _compelling him.

It was different than the feel of his. It was impressive, and velvety, rigid under his fingers. He pumped it lightly, watching the way the skin of it moved as if a different element—like a water on a snowy day that moved slow and imperceptible to the human eye.

Toothless' claw had curled around Hiccup's thin biceps then, lifting the boy fluently. He brought Hiccup to his eye level, an impossible stare that knew more than people gave it credit for, and let out a rumble. Before Hiccup could decipher it, the dragon had flipped him around, and the redhead was on hands and knees. "What?" he breathed. Toothless' answer was a tongue lapping its way down the length of Hiccup's spine. He bowed at the slick and warm path created by the creature's naturally clever muscle. It dipped into the cleft of his rounded cheeks in what could have been termed 'coy'.

Hiccup nearly bolted up right, but the rugged breath of the dragon gave him pause. Toothless was waiting. He would go no further until his master wanted to. Self-conscious, he dropped his head; barely peeking underneath his russet bangs, he bit his lip in thought. The decision was out of his hands now. He knew there would be no turning back from what they were doing. "We have already gone this far," Hiccup whispered. "We might as well finish what we started."

Toothless ecstatically agreed, his tongue darting out and caressing the trembling entrance before him. The pointed end was twisting into the hole. Hiccup mewled at the invasion of his most private place. He bent as he was stretched by the surging thrusts. Shaking, he tensed up, whole body willing for something else, impatient for another treat. His body did not wait long. Toothless, apparently at his limit, drew back.

The immense wings quivered, opening of their own accord, rising up. Toothless never looked more terrifying… yet Hiccup wasn't afraid. No, he was merely waiting, anxious to be satisfied. Amazingly, the dragon's front claws hooked under the human's stomach, gently lifting him upwards, aligning their different bodies as if instinctual. The hooked head of Toothless' member entered carefully, and his wings flapped in place unhurried. Hiccup gasped, while the Night Fury purred in low trills.

When he was fully inside Hiccup, Toothless steadied himself, digging his hind legs into the ground. As the boy grew use to the feel, his writhing lessened considerably. The dragon rocked into the boy, and Hiccup cried out. Toothless' ears flattened against his head and he growled, plunging into the human with little mercy. The feel of the slippery organ filling him so completely had Hiccup dizzy, and he was quickly loosing all other feeling besides the wondrous one building deep within him. Then, there was a new direction, or shift, and suddenly Toothless was brushing against a sensitive spot along his inner walls. Hiccup's body rippled in a contraction of pleasure. The dragon increased his harried pace, coming down upon that sensitive spot again and again and again. Hiccup could take no more, and was shoved over the proverbial cliff. Blinded by bursts of exquisite color and saturated in bliss, Hiccup came. Toothless roared as the too taunt, too welcoming body under him made him release as well.

Both were too spent to move a muscle. By the time they regained any strength, the sun was setting, dimming the already hoary world around them. Hiccup and Toothless had to sneak into the village at dark, the creature hiding his naked, limping master with warm and soothing wings. After that, though? Well, Stoic and Astrid of course suspect things—things Hiccup didn't use to think about—but _that_ is really between master and dragon.


End file.
